6 ms·

I had this problem repeatedly with both Google and Microsoft, though never at the same time and never, so far as I could tell, for the same reason. Everything

I had this problem repeatedly with both Google and Microsoft, though never at the same time and never, so far as I could tell, for the same reason. Everything was set up properly. The domains I hosted had IPv4 and IPv6 addresses with forward and reverse DNS matching exactly. SPF was set perfectly, according to multiple test sites. DKIM was always used and always validated, again according to multiple test sites. I even signed up for a DMARC endpoint account at report-uri.com. Didn't matter. Messages would be spontaneously rejected, sometimes in mid-conversation (this happened to my wife quite a lot). Other times, the remote end would claim to accept the message and then it would disappear into the great bit bucket in the sky. It would be like this for a day or two then spontaneously go back to working. I finally gave up and switched entirely over to Fastmail awhile back. No more delivery problems, but no more self-hosting my own e-mail, something I'd done for twenty years prior (my domain is older than Mozilla and Google).

hardwaresofton 5y ago
> I finally gave up and switched entirely over to Fastmail awhile back. No more delivery problems, but no more self-hosting my own e-mail, something I'd done for twenty years prior (my domain is older than Mozilla and Google). Can anyone speak to what a provider like Fastmail does behind the scenes that guarantees their delivery? Is it the threat to sue/kick up dirt/raise issues with the appropriate regulatory body if perfectly good emails don't go through? Merely having a seat at some sort of regulatory body or committee?
- tallanvor 5y ago
  From what I can tell, there are two main reasons companies like Fastmail don't have these problems. The first is that good email providers spend a lot of time maintaining the reputation of the IP addresses they use and shut down bad actors as quickly as possible. The second is that the more people that use the service, the higher percentage of good quality emails being sent, reducing the effect of the occasional bad actor.
- jraph 5y ago
  I'm self-hosting my mails. Microsoft expects you to send enough mails to consider your mails not as spam. One thing Fastmail does that people who self-host can't is: sending enough mails. I don't know what other measure they may take but this alone probably goes a long way. And yes, this is fucking frustrating. I'm not going to send thousands of mails per months just for the sake of it and don't know how I should do that without spamming. This is so fucked up.
  - hardwaresofton 5y ago
    This is definitely something I've never heard of, thanks for mentioning it -- I had no idea there was such a consideration (or even that it would be a good way to filter out scammers)
- hippari 5y ago
  I think it's likely that they directly share an allow list of each other's server to form some sort of network of email providers.
ergot_vacation 5y ago
Hasn't it been common knowledge for over a decade now that self-hosting email isn't "allowed" in practical terms? Sure, you can put up the server, but most people are on one of the big providers, and chances are they've got your IP range blocked, because nearly every IP range you might be using has probably been owned by spammers at some point. Email was actually one of the first aspects of the "classic" Internet to fall to the gentrification of the tech monopolies, long before the web in general. In theory, it's an open ecosystem anyone can jump into. In reality, unless you have a lot of energy/time/money to get around the big providers banning you for "spam," it's not going to happen. To be fair, I was also surprised to read that anyone was still using Hotmail, so maybe I just don't have my finger on the pulse of the hip new generation.
- Scoundreller 5y ago
  I spotted someone in the wild using a netzero email address this month as their day-to-day.
- gerdesj 5y ago
  "Hasn't it been common knowledge for over a decade now that self-hosting email isn't "allowed" in practical terms?" Not for me and loads of my tiny and not so tiny customers. Just keep your nose clean and follow the rules. This is in the UK, elsewhere ymmv.
  - rstuart4133 5y ago
    FWIW, not for me either. I run mail servers for a small(ish) organisation. In fact, I'd say it's getting easier, not harder. There was a time when fairly arbitrary rules were applied (like "thou shall not send email from a dialup IP Address). They seem to have mostly gone now, and when they are still in place you can just self report via a web form you are not being naughty and it's all good. But you do have to keep your nose clean. Do not send SPAM, under any circumstances. Sounds easy, and indeed it is easy if you are just running a mail server for an organisation where all mail you are sending is generated by people within that organisation. But if you are doing something that involves relaying emails, eg something like running a mailing list, it becomes harder. To give an example - I run a mail server for a club of maybe 20 people. All email is strictly policed, eg you have to sign up, all sign ups are reviewed by a human, including any email asking to sign up. All good right? Nope, because the club has to have at least one email address (say for the secretary) that does not involve signing up. Those emails are all moderated of course - but you are notified of emails waiting for moderation via email. Those notifications contain snippets of the original. If one of the moderators has a GMail account, those snippets triggering SPAM filters can get your server banned by google. The solution is to run a imap server for secretary@ and get them to fetch it manually. Bypass Google for all relayed email in other words. So you have to follow the rules and it's not always obvious what you have to do to follow the rules, but it ain't impossible, and in fact once you know what the rules are it isn't even hard. Any capable sysadmin could do it.

hardwaresofton 5y ago

> I finally gave up and switched entirely over to Fastmail awhile back. No more delivery problems, but no more self-hosting my own e-mail, something I'd done for twenty years prior (my domain is older than Mozilla and Google). Can anyone speak to what a provider like Fastmail does behind the scenes that guarantees their delivery? Is it the threat to sue/kick up dirt/raise issues with the appropriate regulatory body if perfectly good emails don't go through? Merely having a seat at some sort of regulatory body or committee?

tallanvor 5y ago
From what I can tell, there are two main reasons companies like Fastmail don't have these problems. The first is that good email providers spend a lot of time maintaining the reputation of the IP addresses they use and shut down bad actors as quickly as possible. The second is that the more people that use the service, the higher percentage of good quality emails being sent, reducing the effect of the occasional bad actor.
jraph 5y ago
I'm self-hosting my mails. Microsoft expects you to send enough mails to consider your mails not as spam. One thing Fastmail does that people who self-host can't is: sending enough mails. I don't know what other measure they may take but this alone probably goes a long way. And yes, this is fucking frustrating. I'm not going to send thousands of mails per months just for the sake of it and don't know how I should do that without spamming. This is so fucked up.
- hardwaresofton 5y ago
  This is definitely something I've never heard of, thanks for mentioning it -- I had no idea there was such a consideration (or even that it would be a good way to filter out scammers)
hippari 5y ago
I think it's likely that they directly share an allow list of each other's server to form some sort of network of email providers.

ergot_vacation 5y ago

Hasn't it been common knowledge for over a decade now that self-hosting email isn't "allowed" in practical terms? Sure, you can put up the server, but most people are on one of the big providers, and chances are they've got your IP range blocked, because nearly every IP range you might be using has probably been owned by spammers at some point. Email was actually one of the first aspects of the "classic" Internet to fall to the gentrification of the tech monopolies, long before the web in general. In theory, it's an open ecosystem anyone can jump into. In reality, unless you have a lot of energy/time/money to get around the big providers banning you for "spam," it's not going to happen. To be fair, I was also surprised to read that anyone was still using Hotmail, so maybe I just don't have my finger on the pulse of the hip new generation.

Scoundreller 5y ago
I spotted someone in the wild using a netzero email address this month as their day-to-day.
gerdesj 5y ago
"Hasn't it been common knowledge for over a decade now that self-hosting email isn't "allowed" in practical terms?" Not for me and loads of my tiny and not so tiny customers. Just keep your nose clean and follow the rules. This is in the UK, elsewhere ymmv.
- rstuart4133 5y ago
  FWIW, not for me either. I run mail servers for a small(ish) organisation. In fact, I'd say it's getting easier, not harder. There was a time when fairly arbitrary rules were applied (like "thou shall not send email from a dialup IP Address). They seem to have mostly gone now, and when they are still in place you can just self report via a web form you are not being naughty and it's all good. But you do have to keep your nose clean. Do not send SPAM, under any circumstances. Sounds easy, and indeed it is easy if you are just running a mail server for an organisation where all mail you are sending is generated by people within that organisation. But if you are doing something that involves relaying emails, eg something like running a mailing list, it becomes harder. To give an example - I run a mail server for a club of maybe 20 people. All email is strictly policed, eg you have to sign up, all sign ups are reviewed by a human, including any email asking to sign up. All good right? Nope, because the club has to have at least one email address (say for the secretary) that does not involve signing up. Those emails are all moderated of course - but you are notified of emails waiting for moderation via email. Those notifications contain snippets of the original. If one of the moderators has a GMail account, those snippets triggering SPAM filters can get your server banned by google. The solution is to run a imap server for secretary@ and get them to fetch it manually. Bypass Google for all relayed email in other words. So you have to follow the rules and it's not always obvious what you have to do to follow the rules, but it ain't impossible, and in fact once you know what the rules are it isn't even hard. Any capable sysadmin could do it.